CN106867601A - A kind of diesel antiwear additive and preparation method thereof - Google Patents

A kind of diesel antiwear additive and preparation method thereof Download PDF

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Publication number
CN106867601A
CN106867601A CN201710145070.XA CN201710145070A CN106867601A CN 106867601 A CN106867601 A CN 106867601A CN 201710145070 A CN201710145070 A CN 201710145070A CN 106867601 A CN106867601 A CN 106867601A
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China
Prior art keywords
oleic acid
parts
acid
antiwear additive
continue
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Pending
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CN201710145070.XA
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Chinese (zh)
Inventor
王召光
王芸云
王占新
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YIXING CITY XINGGUANG BAOYI CHEMICAL Co Ltd
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YIXING CITY XINGGUANG BAOYI CHEMICAL Co Ltd
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Priority to CN201710145070.XA priority Critical patent/CN106867601A/en
Publication of CN106867601A publication Critical patent/CN106867601A/en
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1826—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms poly-hydroxy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof

Abstract

The invention discloses a kind of diesel antiwear additive, including following parts by weight component：60 ~ 100 parts of oleic acid, 20 ~ 60 parts of C2 C6 polyalcohols, 10 ~ 20 parts of graphene oxide.Meanwhile, the invention also discloses the preparation method of above-mentioned antiwear additive., without any pollution, environment protecting is good, while improving oil quality, the effect propety to Diesel engine is significantly improved, so as to dramatically reduce the consumption of fossil feedstock for the present invention.

Description

A kind of diesel antiwear additive and preparation method thereof
Technical field
The invention belongs to PETROLEUM PROCESSING field, and in particular to a kind of diesel antiwear additive and preparation method thereof.
Background technology
Cleaning the production of diesel oil makes diesel oil have the notable spies such as sulfur content is low, arene content is low, Cetane number is high, cut is light Point.Due to generally employing more harsh hydrogenation technique in the production process for cleaning diesel oil, cause to clean the polarity in diesel oil Compounds content reduction, polycyclic, double ring arene content is accordingly reduced, thus reduces the natural greasy property of diesel oil, is caused There is abrasion in injection pump, reduces its service life.
Antiwear additive is added in diesel oil, also known as diesel fuel lubricity modifier, is below stated referred to as：Diesel antiwear additive.It is letter Just one of method of diesel fuel lubricity performance is effectively improved, is also current international widely used effective measures.The current world is major Oil company and specialized company are all developing, are producing the lubricity improver of adaptation commercialization diesel oil needs.
At present, China's diesel oil it is main by straight-run diesel oil, hydrogenation of total effluent diesel oil, diesel oil hydrogenation diesel oil and it is a small amount of in Pressure hydrogenated diesel oil is constituted.Some polar emollient components, but its sulfur content are remained in diesel oil about 0.2% or so, it is impossible to adapt to The requirement of the sustainable recycling economy development of society.
The content of the invention
Goal of the invention：The purpose of the present invention is to solve the shortcomings of the prior art, there is provided a kind of diesel antiwear additive.
Preparation method another object of the present invention is to provide above-mentioned diesel antiwear additive.
Technical scheme：In order to reach foregoing invention purpose, the present invention is specifically achieved like this：A kind of diesel oil is wear-resistant Agent, including following parts by weight component：60 ~ 100 parts of oleic acid, 20 ~ 60 parts of C2-C6 polyalcohols, 10 ~ 20 parts of oxidation stone Black alkene.
A kind of preferred scheme, is made up of the component of following parts by weight：80 parts of oleic acid, 30 parts of glycerine and 10 parts Graphene oxide.
Wherein, the oleic acid is soybean oleic acid, palmitoleic acid, oleic acid, linoleic acid, leukotrienes, tall oil acid, tristearin One or more mixing in acid.
Wherein, the C2-C6 polyalcohols are ethylene glycol, propane diols, glycerine, isopropanol or pentaerythrite.
Wherein, the graphene oxide is replaced by hexahydrotoluene.
A kind of preparation method of diesel antiwear additive, comprises the following steps：
（1）Oleic acid is dehydrated, until oleic acid moisture content is less than 5%；
（2）Oleic acid is distilled, temperature control is in 120 ~ 160 DEG C, 4 ~ 10 hours reaction time；
（3）Oleic acid after heating is cooled to room temperature, and is freezed at -5 ~ -15 DEG C, continue 3 ~ 12 hours, to solid oil Saturated acid mass ratio in acid is less than 2.5%, forms oleic acid solid；
（4）Solid oleic acid after freezing is heated to 160 DEG C of dissolvings, is dehydrated again, until moisture content is less than 1%；
（5）To polyalcohol and graphene oxide is added in oleic acid, 250 DEG C are heated to, continue to carry out esterification in 4 ~ 6 hours；
（6）Step（5）Room temperature being naturally cooled to after completion of the reaction, and being freezed again, control -15 DEG C of temperature, 4 ~ 8 hours i.e. .
Wherein, the step（3）In when being freezed to oleic acid, be first refrigerated to -5 DEG C, continue 1 ~ 4 hour, continue to freeze To -10 DEG C, continue 1 ~ 4 hour, be finally refrigerated to -15 DEG C, continue 1 ~ 4 hour.
A key point in the present invention is using graphene oxide as catalyst, due to graphene oxide molecule simultaneously It is with carboxylic acid group and hydroxyl therefore extremely outstanding as catalyst Use Limitation fruit, and graphene oxide molecule is symmetrical junction Structure, very stable in whole course of reaction, intermediate existence time is of short duration, redox efficiency high；And hexahydrotoluene conduct When catalyst replaces graphene oxide, its structure is more more symmetrical than graphene oxide, more stable during the course of the reaction, but due to Its redox is completed on its methyl, thus catalytic efficiency ratio use graphene oxide when it is low, the time will be grown.
Another key is freezing processing twice in the present invention, and first time freezing processing is pretreatment oleic acid, in order to ensure The mass ratio of saturated acid is controlled below 2.5%, prevents from being subsequently generated more polyunsaturated fatty acid ester, using gradually lowering the temperature, effect More preferably；Second freezing processing is after completion of the esterification reaction, it is therefore an objective to the mono-stearin and saponified of elimination reaction generation, but Because mono-stearin and saponified freezing point and the freezing point of unsaturated fat ester are mutually gone larger, therefore it is using disposable cooling Can reach separation purpose.
Beneficial effect：The present invention has the following advantages that compared with conventional art：
1st, acid number is low, to diesel oil acidity and alkaline matter without any harm risk；
When the 2nd, adding diesel oil to use compared with acid type agent using effect more preferably, addition is smaller, great economy；
3rd, in product hydrophilic radical change, it is ensured that product is obtained to the guarantee performance of diesel quality index in use Improve；
4th, without any pollution, environment protecting is good, while improving oil quality, the effect propety to Diesel engine is substantially carried Height, so as to dramatically reduce the consumption of fossil feedstock.
Specific embodiment
Embodiment 1：
Take the oleic acid of 70 parts of parts by weight（Soybean oleic acid）, 30 parts of ethylene glycol, 12 parts of graphene oxide is stand-by, and oleic acid is entered Row dehydration, until oleic acid moisture content is less than 5%, distills to oleic acid, and temperature control is at 120 ~ 160 DEG C, and the reaction time 4 ~ 10 is small When, the oleic acid after heating is cooled to room temperature, and freezed at -5 ~ -15 DEG C, continue 3 ~ 12 hours, into solid oleic acid Saturated acid mass ratio be less than 2.5%, formed oleic acid solid, by the solid oleic acid after freezing be heated to 160 DEG C dissolving, take off again Water, until moisture content is less than 1%, to C2-C6 polyalcohols and graphene oxide is added in oleic acid, is heated to 250 DEG C, continues 4 ~ 6 small Shi Jinhang esterifications, naturally cool to room temperature after completion of the reaction, and are freezed again, control -15 DEG C of temperature, 4 ~ 8 hours Obtain final product.
Embodiment 2：
Take the oleic acid of 60 parts of parts by weight（Palmitoleic acid）, 20 parts of propane diols, 10 parts of graphite oxide will be stand-by, and oleic acid is entered Row dehydration, until oleic acid moisture content is less than 5%, distills to oleic acid, and temperature control is at 120 ~ 160 DEG C, and the reaction time 4 ~ 10 is small When, the oleic acid after heating is cooled to room temperature, and freezed at -5 ~ -15 DEG C, continue 3 ~ 12 hours, into solid oleic acid Saturated acid mass ratio be less than 2.5%, formed oleic acid solid, by the solid oleic acid after freezing be heated to 160 DEG C dissolving, take off again Water, until moisture content is less than 1%, to C2-C6 polyalcohols and graphene oxide is added in oleic acid, is heated to 250 DEG C, continues 4 ~ 6 small Shi Jinhang esterifications, naturally cool to room temperature after completion of the reaction, and are freezed again, control -15 DEG C of temperature, 4 ~ 8 hours Obtain final product.
Embodiment 3：
Take the oleic acid of 100 parts of parts by weight（Oleic acid）, 60 parts of glycerine, 20 parts of graphene oxide is stand-by, by oleic acid It is dehydrated, until oleic acid moisture content is less than 5%, oleic acid is distilled, temperature control is in 120 ~ 160 DEG C, reaction time 4 ~ 10 Hour, the oleic acid after heating is cooled to room temperature, and freezed at -5 ~ -15 DEG C, continue 3 ~ 12 hours, to solid oleic acid In saturated acid mass ratio be less than 2.5%, formed oleic acid solid, by the solid oleic acid after freezing be heated to 160 DEG C dissolving, again Dehydration, until moisture content is less than 1%, to C2-C6 polyalcohols and graphene oxide is added in oleic acid, is heated to 250 DEG C, continues 4 ~ 6 Hour carries out esterification, and room temperature is naturally cooled to after completion of the reaction, and is freezed again, controls -15 DEG C of temperature, and 4 ~ 8 is small When obtain final product.
Embodiment 4：
Take the oleic acid of 80 parts of parts by weight（Linoleic acid, flax acid blend）, 50 parts of isopropanol, 16 parts of hexahydrotoluene treats With, oleic acid is dehydrated, until oleic acid moisture content be less than 5%, oleic acid is distilled, temperature control at 120 ~ 160 DEG C, instead 4 ~ 10 hours between seasonable, the oleic acid after heating is cooled to room temperature, and is freezed at -5 ~ -15 DEG C, continue 3 ~ 12 hours, Saturated acid mass ratio into solid oleic acid is less than 2.5%, forms oleic acid solid, and the solid oleic acid after freezing is heated into 160 DEG C Dissolving, is dehydrated again, until moisture content is less than 1%, to C2-C6 polyalcohols and graphene oxide is added in oleic acid, is heated to 250 DEG C, continue to carry out esterification in 4 ~ 6 hours, room temperature is naturally cooled to after completion of the reaction, and freezed again, control temperature- 15 DEG C, obtain final product within 4 ~ 8 hours.
Embodiment 5：
Take the oleic acid of 90 parts of parts by weight（Palmitoleic acid, tall oil acid, stearic acid mixing）, 55 parts of pentaerythrite, 18 parts Graphene oxide is stand-by, and oleic acid is dehydrated, until oleic acid moisture content is less than 5%, oleic acid is distilled, and temperature control exists 120 ~ 160 DEG C, in 4 ~ 10 hours reaction time, the oleic acid after heating is cooled to room temperature, and is freezed at -5 ~ -15 DEG C, held Continuous 3 ~ 12 hours, the saturated acid mass ratio into solid oleic acid is less than 2.5%, oleic acid solid is formed, by the solid oleic acid after freezing 160 DEG C of dissolvings are heated to, are dehydrated again, until moisture content is less than 1%, to addition C2-C6 polyalcohols and graphite oxide in oleic acid Alkene, is heated to 250 DEG C, continues to carry out esterification in 4 ~ 6 hours, and room temperature is naturally cooled to after completion of the reaction, and carries out again cold Freeze, control -15 DEG C of temperature, obtain final product within 4 ~ 8 hours.

Claims (7)

1. a kind of diesel antiwear additive, it is characterised in that the component including following parts by weight：60 ~ 100 parts of oleic acid, 20 ~ 60 parts C2-C6 polyalcohols, 10 ~ 20 parts of graphene oxide.
2. diesel antiwear additive according to claim 1, it is characterised in that be made up of the component of following parts by weight：80 parts Oleic acid, 30 parts of glycerine and 10 parts of graphene oxide.
3. diesel antiwear additive according to claim 1 and 2, it is characterised in that the oleic acid is soybean oleic acid, palm oil One or more mixing in acid, oleic acid, linoleic acid, leukotrienes, tall oil acid, stearic acid.
4. diesel antiwear additive according to claim 1 and 2, it is characterised in that the C2-C6 polyalcohols are ethylene glycol, third Glycol, glycerine, isopropanol or pentaerythrite.
5. diesel antiwear additive according to claim 1, it is characterised in that the graphene oxide is by hexahydrotoluene generation Replace.
6. the preparation method of any diesel antiwear additive of claim 1 ~ 5, it is characterised in that comprise the following steps：
（1）Oleic acid is dehydrated, until oleic acid moisture content is less than 5%；
（2）Oleic acid is distilled, temperature control is in 120 ~ 160 DEG C, 4 ~ 10 hours reaction time；
（3）Oleic acid after heating is cooled to room temperature, and is freezed at -5 ~ -15 DEG C, continue 3 ~ 12 hours, to solid oil Saturated acid mass ratio in acid is less than 2.5%, forms oleic acid solid；
（4）Solid oleic acid after freezing is heated to 160 DEG C of dissolvings, is dehydrated again, until moisture content is less than 1%；
（5）To polyalcohol and graphene oxide is added in oleic acid, 250 DEG C are heated to, continue to carry out esterification in 4 ~ 6 hours；
（6）Step（5）Room temperature being naturally cooled to after completion of the reaction, and being freezed again, control -15 DEG C of temperature, 4 ~ 8 hours i.e. .
7. the preparation method of diesel antiwear additive according to claim 6, it is characterised in that the step（3）In to oleic acid When being freezed, -5 DEG C are first refrigerated to, continue 1 ~ 4 hour, continue to be refrigerated to -10 DEG C, continue 1 ~ 4 hour, be finally refrigerated to -15 DEG C, continue 1 ~ 4 hour.
CN201710145070.XA 2017-03-13 2017-03-13 A kind of diesel antiwear additive and preparation method thereof Pending CN106867601A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109929624A (en) * 2019-04-25 2019-06-25 上海鑫灵精细化工有限公司 A kind of constituent and preparation method of fatty acid diesel antiwear additive

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002061018A1 (en) * 2001-02-01 2002-08-08 Shibin Hu Fuel oil additive and fuel oil product comprising the fuel oil additive
CN102965201A (en) * 2012-12-12 2013-03-13 中国科学院长春应用化学研究所 Preparation method of diesel antiwear agent
CN103418383A (en) * 2013-08-23 2013-12-04 江苏科技大学 Magnetic nanometer oxidized graphene and preparation method and application thereof
CN104293414A (en) * 2014-07-21 2015-01-21 宜兴市星光宝亿化工有限公司 Fatty acid ester type diesel oil antiwear agent and preparation method thereof
CN104946404A (en) * 2015-05-21 2015-09-30 沧州嘉泰油脂有限公司 Production technology of stearic acid and oleic acid

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002061018A1 (en) * 2001-02-01 2002-08-08 Shibin Hu Fuel oil additive and fuel oil product comprising the fuel oil additive
CN102965201A (en) * 2012-12-12 2013-03-13 中国科学院长春应用化学研究所 Preparation method of diesel antiwear agent
CN103418383A (en) * 2013-08-23 2013-12-04 江苏科技大学 Magnetic nanometer oxidized graphene and preparation method and application thereof
CN104293414A (en) * 2014-07-21 2015-01-21 宜兴市星光宝亿化工有限公司 Fatty acid ester type diesel oil antiwear agent and preparation method thereof
CN104946404A (en) * 2015-05-21 2015-09-30 沧州嘉泰油脂有限公司 Production technology of stearic acid and oleic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109929624A (en) * 2019-04-25 2019-06-25 上海鑫灵精细化工有限公司 A kind of constituent and preparation method of fatty acid diesel antiwear additive

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Application publication date: 20170620